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2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → 5-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 245775
ノート
印刷プレビュー

反応式

HRID 245775 の反応式
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5].C([Mg]Cl)C.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[CH:33]=[C:32]([C:34](OC)=[O:35])[N:31]([CH3:38])[C:28]2=[CH:29][N:30]=1>O1CCCC1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[CH:33]=[C:32]([C:34]([NH:5][C:4]3[CH:6]=[CH:7][C:8]([B:10]4[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]4)=[CH:9][C:3]=3[O:2][CH3:1])=[O:35])[N:31]([CH3:38])[C:28]2=[CH:29][N:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67366332methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylateHCID 178461633HCID 178461633、化合物

生成物 1

HCID 673637125-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide収率 60.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
3 回

実験手順

To 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.09 g, 8.37 mmol) in tetrahydrofuran (20 ml) under a nitrogen atmosphere was added ethylmagnesium chloride, 2.0 M in tetrahydrofuran (4.19 ml, 8.37 mmol) and the mixture was heated at reflux for one hour. To the warm reaction was added methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (878 mg, 3.99 mmol) in tetrahydrofuran (10 ml) and the resulting mixture was heated overnight. Then the reaction mixture was cooled to room temperature and concentrated. The residue was taken up in ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was coated on hydromatrix and purified by flash chromatography (gradient of heptane to heptane/ethyl acetate 1/1) to give 5-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (1.05 g).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. customTo the warm reaction
  4. temperaturethe resulting mixture was heated overnight
  5. concentrationconcentrated
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with ethyl acetate twice
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. custompurified by flash chromatography (gradient of heptane to heptane/ethyl acetate 1/1)

出典と根拠

ORDレコード
ord-bbd0b44c3fb74cf19ccfc43c49ec8ea0
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658794B2

反応ノート

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